Ethyl 3-iodo-1H-indole-2-carboxylate

Base Information

• Chemical Name: Ethyl 3-iodo-1H-indole-2-carboxylate
• CAS No.: 117637-79-3
• Molecular Formula: C11H10INO2
• Molecular Weight: 315.11
• Hs Code.: 2933990090
• UNII: N9XH8S7DYS
• DSSTox Substance ID: DTXSID70446996
• Nikkaji Number: J910.223J
• Wikidata: Q82265764
• Mol file: 117637-79-3.mol

Synonyms:Ethyl 3-iodo-1H-indole-2-carboxylate;117637-79-3;1H-Indole-2-carboxylic acid, 3-iodo-, ethyl ester;N9XH8S7DYS;3-iodoindole-2-carboxylic acid ethyl ester;ethyl 3-iodoindole-2-carboxylate;Ethyl-3-iodo-1H-indole-2-carboxylate;UNII-N9XH8S7DYS;3-Iodo-1H-indole-2-carboxylic acid ethyl ester;2-ethoxycarbonyl-3-iodoindole;SCHEMBL2724382;DTXSID70446996;BZVJUWYDEMOJMH-UHFFFAOYSA-N;MFCD18157645;AKOS015853667;AF-0703;CS-0374521;FT-0682725;E83953;10.14272/BZVJUWYDEMOJMH-UHFFFAOYSA-N.1;10.14272/BZVJUWYDEMOJMH-UHFFFAOYSA-N.2;doi:10.14272/BZVJUWYDEMOJMH-UHFFFAOYSA-N.1;doi:10.14272/BZVJUWYDEMOJMH-UHFFFAOYSA-N.2;W-204952

Chemical Property of Ethyl 3-iodo-1H-indole-2-carboxylate

Chemical Property:

• PSA: 42.09000
• LogP: 2.94920
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 314.97563
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl 3-iodo-1H-indole-2-carboxylate >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=CC=CC=C2N1)I

Technology Process of Ethyl 3-iodo-1H-indole-2-carboxylate

There total 2 articles about Ethyl 3-iodo-1H-indole-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-carbethoxyindole (3770-50-1,117770-52-2) → ethyl 3-iodo-1H-indole-2-carboxylate (117637-79-3)

Guidance literature:

With potassium hydroxide; iodine; In water; N,N-dimethyl-formamide; for 0.5h; Ambient temperature;

Reference yield:

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → ethyl 3-iodo-1H-indole-2-carboxylate (117637-79-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 24 h / Inert atmosphere; Reflux

2: N-chloro-succinimide; sodium iodide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With N-chloro-succinimide; sulfuric acid; sodium iodide; In N,N-dimethyl-formamide;

DOI:10.1021/jo201528u

Reference yield: 99.0%

ethyl 3-iodo-1H-indole-2-carboxylate (117637-79-3) + phenylboronic acid (98-80-6) → ethyl 3-phenyl-1H-indole-2-carboxylate (37129-23-0)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In ethanol; water; toluene; for 48h; Heating / reflux;

upstream raw materials:

2-carbethoxyindole

Indole-2-carboxylic acid

Downstream raw materials:

ethyl 3-phenylethynylindole-2-carboxylate

3-iodo-1-(phenylmethyl)-1H-indole-2-carboxylic acid ethyl ester

ethyl 1-(benzenesulfonyl)-1H-3-iodoindole-2-carboxylate

1-(3-cyanophenyl)-3-iodoindole-2-carboxylic acid ethyl ester

Refernces

• 1、 Fu, Jian,Hammoud, Sokaina,Kremer, Laurent,Maaliki, Carine,Raynaud, Clément,Thibonnet, Jér?me,Thiery, Emilie,Viljoen, Albertus,Villaume, Sydney,Vincent, Stéphane P.. "Synthesis and evaluation of heterocycle structures as potential inhibitors of Mycobacterium tuberculosis UGM". . . Retrieved 2020.
• 2、 Vela, Marta,García-Gimeno, María Adelaida,Sanchis, Ana,Bono-Yagüe, José,Cumella, José,Lagartera, Laura,Pérez, Concepción,Priego, Eva-María,Campos, Angela,Sanz, Pascual,Vázquez-Manrique, Rafael P.,Castro, Ana. "Neuroprotective Effect of IND1316, an Indole-Based AMPK Activator, in Animal Models of Huntington Disease". . p. 275 - 287. Retrieved 2022/01/15.
• 3、 Jiang, Xuefeng,Li, Yiming,Lu, Lingling. "Visible-light-promoted oxidative halogenation of (hetero)arenes". supporting information. p. 5989 - 5994. Retrieved 2020/10/18.